Do Not Pass Go
by psychochick1
Summary: Even the most ironclad contracts can have hidden escape clauses, exploitable with proper documentation.


It wasn't as if Sam expected it to work. In fact, that was the farthest thing from his mind when he first saw it. With only a little over two months to go before Dean's deal came due, Sam was in a transitional mindset between feverishly working on ways to break the deal and a creeping sense of despair that maybe there was nothing left to try. He lived in a place where hysteria could sometimes manifest.

He wasn't even looking for it when it came his way. He and Dean were holed up in a motel in Idaho, tracking a poltergeist wrecking havoc in a housing community. Dean had just gone for coffee, and while he waited Sam fired up the laptop, automatically checking his email in hopes of getting miraculous news from one of his contacts.

Skimming quickly, he found little of interest and was about to log out when a small subject header caught his eye.

"Get Out Of Hell Free!"

His hand jerked involuntarily, clicking the link before his brain really caught up to what he was reading. The tiny flare of useless hope that had ignited at the sight of the words quickly died. Nothing more than a joke. "Gotcha" cards to hand out to judgmental idiots. No answers were to be had there, only chuckles from people who had no idea about the realities of hell.

Still, at a second glance even Sam couldn't stop a small smile from curling up the edges of his mouth. There _was_ something vaguely humorous about the "Get Out of Hell Free" cards. Oddly appropriate for them, considering the back of the plastic card read, "Works for All 7+1 Sins: Sloth, Pride, Wrath, Lust, Gluttony, Greed, Envy . . . and Stupidity."

Sam snorted. If only it was that easy. If only the hellfire could be avoided as easily as jumping over them, as the little mustached guy did in the illustrations under the smaller words, _This Card May be Kept Until Needed or Sold. _The resemblance to the Monopoly card brought a sudden rush of warm almost-forgotten memories.

_They were in Minnesota for nearly three months in the winter when Sam was eight, and a huge snowstorm closed everything down for three days. John was home with the boys, all three of them snowed in. The whole apartment was cleaned by the end of the first day, the weapons in flawless condition by lunch the second day, and after that Sammy started going stir-crazy._

_He didn't know where Dean unearthed it, but his big brother pulled out a Monopoly game and managed to coerce Dad into playing with them. After teaching Sammy the rules and going over the money, the game was on. _

_John didn't believe in letting the boys win, but that was okay. Sam turned out to be ruthless at real estate, acquiring property and building on it just before Dean or John landed on it. He got in some trouble as the game went on, landing on John's row of hotels, then was sent to jail three times in a row. Sammy didn't like to be sent to jail; even though it was only a game, he knew that jail was a bad place and he needed to get out. His money was running low, and he couldn't seem to roll doubles. Finally, he paid the bail and got out, only to pick up a Chance card that sent him right back._

_As Dean went to take his turn, he glanced over and saw Sam's stricken face and welling eyes. Looking down, he gave a little sigh and picked up the orange card he had drawn earlier in the game. "Hey Sammy, here."_

_Sam took the card and looked at it curiously – "Get out of Jail Free." _

"_I'm bailing you out," Dean explained._

_Sammy grinned up at his brother and moved his token to the edge of the board – Just Visiting. Dean would always bail him out. That's what big brothers did. _

Yeah, that's what big brothers did, or rather what Dean did. Always bailed Sam out, even at the cost of his own soul.

Sam clenched his jaw, his determination renewed afresh. It was his turn to bail his brother out now, and he wouldn't rest, right up until the last moment, to save Dean from hell.

Seized by an odd fit of dark humor, Sam looked at the cards again, then clicked on the PayPal button. There really wasn't anything funny about their situation, but if Sam could appreciate the gallows chuckle, he knew Dean would too.

* * *

Three hundred and sixty-five days (plus an extra day – hey, if you only have a year to live, make sure it falls on a leap year) after Dean voluntarily made out with a demon, he found himself in freefall. 

But only temporarily.

Dean cursed in three languages when he landed painfully on the dark rock. Okay, that had sucked.

"Fucking hellhounds," he muttered, rubbing the phantom ache of sharp teeth in his chest as he stood up and looked around. Between the eye-hurting murky light and hovering mists, this had to be the gloomiest place he'd ever seen; considering he normally lurked around cemeteries and haunted houses, that was saying something.

Well, it was Hell. What had he expected?

Maybe a bit more fire and brimstone. He was actually rather disappointed at the lack of fire and brimstone, to tell the truth. Nothing says "You're in Hell!" quite like a blazing inferno and choking fumes.

This looked like a bad special effects reject of a haunted swamp. So far, Hell was disappointing.

From what he could see in the dim light, Dean was standing in a vast cavern near the shores of a sluggish river. The jagged rock wall at his back threatened to shred his skin at the lightest touch, but the shores had been worn slick-smooth by the river, which oozed along its course with the consistency of congealed blood. He wasn't entirely sure it _wasn't_blood, judging from the putrid smell.

Even when squinting across the river towards the source of the light, Dean could barely make out the far shore. A giant figure crouched there, silhouetted as a shadow against a deeper black, back end still but front end undulating with a weird sort of motion. What the hell was that?

Movement at its feet dragged his gaze down to something emerging from the deeper shadows and moving slowly on the water. A faint shape drifted closer, gradually taking form out of the mists into a skeletal man on a boat, poling towards the shore.

Dean took a closer look around his side of the river. Further down the bank, a line of people stood watching, waiting for the boatman. Some were calm, others were pacing, and a couple were sitting down, full-out pouting. Beyond them, a huddled mass of miserable bastards were scattered around, some crouched close to the jagged walls and looking as ragged and worn as the boatman's robes.

Huh. Dean stuck his hands in his pockets as he considered the situation. Looks like the Greeks might've got it right.

Shrugging to himself, he picked his way down the shore towards the crowd, automatically scanning and classifying people. Couple of hot girls, a bevy of older folks, and a handful of guys in military fatigues. He aimed for the hot girls, an easy choice considering that this might be his last chance to flirt before ending up in Hell, but his approach attracted the attention of a guy in Marine BDUs.

"Hey," Dean nodded at him. "What're you in for?"

"Convoy was ambushed in Iraq. You?"

"Sold my soul."

The Marine stared at him. "What'd you do that for?"

"To save my brother."

"Oh. Gotcha."

Dean glanced out across the river. "Who's that?"

"The Ferryman." The Marine nodded at the boat. "He'll explain the rules. Gotta pack as many people in as he can for each trip, but sometimes you gotta wait your turn. I had to miss the last boat – too many people, y'know? But he takes everyone across in the end as long as you can pay him."

Dean gestured at the ragged group of wary watchers. "What about them? They can't pay?"

The Marine shrugged. "Can't, won't, don't want to, who knows. But why anyone'd want to stay here beats me."

"I hear ya." Even though he wasn't looking forward to the prospect of Hell, Dean knew he wouldn't want to stay on this side of the creepy river. He'd go freaking nuts. "So they'll sort us out on the other side?"

"Yep." The Marine glanced around with a sour look. "Although I have to say that so far the afterlife's not looking exactly like what I expecting."

Dean shrugged. "Hope it gets better for you." He clapped him on the shoulder, then circled around to where the two hot girls, a blonde and a brunette, were watching his approach with smiles on their lips. "Hey, ladies."

"Hi," the blonde said as she did a blatant head-to-toe scan and smiled slyly. "How're you doing?"

The brunette laughed. "He's dead just like we are, Jodi."

"Hey, you may be dead, but you're still looking fine," Dean tried out his best panty-dropper grin, letting his eyes flick over both girls. Yep, being dead didn't detract from either of their assets.

"And we're still lesbians," the brunette said firmly enough, but the way she eyed Dean told him they were probably bisexual with a preference for each other. He couldn't help his grin. Okay, so maybe being dead wasn't all that bad.

He glanced over at the approaching Ferryman, then lowered his voice to a purr. "So girls, I was thinking . . . you wanna wait for the next boat? Y'know, find some extra time to talk, maybe get to know each other?"

The blonde --Jodi -- snorted lightly. "Is this your idea of a last-minute attempt to screw us heathen lesbians straight and thus save our eternal souls?"

Dean wrinkled his nose in disgust. Who came up with that idiotic idea? "What? Of course not! I thought I'd like to watch," he said with a leer. Both ladies burst out in giggles. The sound was deadened by the cloying mists around them, but it was still enough to attract everyone else's attention. Dean looped his arms around the two girls and winked at the people staring at them. _I've still got it, _he congratulated himself.

The Ferryman pulled up to the shore with a grinding crackle of dead bone on rock, and everyone fell deathly silent. Dean dropped his arms and stepped forward instinctively at the sight of the Ferryman's drawn, dead-white face with empty black eyes.

The Ferryman turned his head, seeming to consider all of them gathered at the shore, then nodded once, slowly.

"Welcome to Hades," he intoned in a voice like a cat sharpening its claws on glass. "I am Charon, your Ferryman today. As you are now deceased, this is your recommended form of transport. We are anticipating a slow but uneventful journey across the River Acheron today into the land of the dead."

Dean stared, not quite believing his ears. Was this guy for real?

"Let me go over the rules," Charon screeched on. "These are for your safety, so please follow them. Please remain seated and keep arms and legs inside the boat at all times. If you fall in, it may be some time before someone decides to fish you out. As we make our approach to the other shore, if you stand you may come within range of Cerberus. He has already eaten twice today, but one of his heads is still hungry. Please, no roughhousing on board, no food or drink, and smoking is not allowed until you actually reach Hell, for those of you who have that listed as your final destination."

Charon unfolded a ramp from the side of the boat and let it bang onto the rock. Slowly, he clambered down and stood at the bottom of the gangplank, drawing a pouch out of his robes. "The toll to cross the River Acheron is an_obolus_, or whatever coin you have handy. Sorry, exact change only. No exchanges, returns, or refunds."

There was a pause, then a sudden flurry as people dug in their clothes for their wallets or pockets for spare change. Dean dug his wallet out of his jacket pocket – _huh, I guess you really can take it with you_ – and inspected its contents. He dug through his coins, looking for quarters and hoping Sam hadn't used them all at the Laundromat, when the edge of an orange card caught his eye.

He pulled it out, and smiled. Sam had given him that card only a few weeks back, casually sliding it across the table at dinner one night. At Dean's raised eyebrow, he'd only shrugged in a way that meant _Couldn't hurt_ and offered him a smile tinged with sadness. Dean had accepted the gesture for what it was and slipped the card into his wallet.

_Hmmm. Couldn't hurt. _

Dean shrugged, shared his handful of nickels and dimes with the two lesbians and the Marine, and got in line at the end. Slowly the line shrank as everyone dropped coins in the Ferryman's pouch and walked up the gangplank to find their seats. A couple of people didn't have change and went down the line taking a collection for the fare to get across. Dean glanced back at the group crouched among the rocks, watching them hungrily, and gave away the rest of his pennies, keeping enough for himself just in case.

Finally, it was his turn. Dean watched appreciatively as the girls climbed up the gangplank ahead of him, then went for it. He handed the card to Charon instead of a coin.

Charon's blank eyes stared at him before a skeletal hand reached slowly down to take the card. Bringing it up to his face, he seemed to take forever to read the writing.

Finally he sighed heavily, producing a sound like frigid wind moaning through winter trees. He tilted his head back and called shrilly, "HADES! CUSTOMER SERVICE NEEDED ON THE ACHERON!"

"Uh." Dean took a step back, wide-eyed. Everyone already on the boat looked down at him curiously. He shrugged at them.

There was quiet for several long moments, then a snarl, three sharp barks, and a loud splash. Squinting out across the river, Dean could barely make out the dark shape now swimming towards them, a man seated on its back.

Within minutes, a giant three-headed dog bounded from the river, barking in surround sound. It waited until the man on its back slipped off before shaking vigorously, sending cascades of dark, foul-smelling water everywhere. Dean ducked the worst of it, but heard squeals as the people on the boat were soaked.

Standing, Dean had to look up at a very tall, stern-looking man with dark hair and a chilly demeanor. He gazed down at the young hunter with cold disdain, then turned to the Ferryman. "What is it?"

The Ferryman handed the card to Hades, who touched it as one would handle something contaminated. He scanned it, then fixed an even colder glare at Dean. "Where did you get this?"

"My brother gave it to me," Dean managed, swallowing hard and struggling not to show any fear. Shit, Death really couldn't take a joke.

Hades looked at the card again, then growled, "Wait here."

He strode up the bank, pulling something from his robes and giving it a hard tap. A few seconds later three more people joined him, where they huddled in furious whispered conference. Scrolls were produced and shoved around. A few angry exclamations and flailing arms punctuated the argument.

As he watched them, very confused, Dean suddenly felt a cold touch on the side of his head. He whipped around and found himself face to face with Cerberus. With one of the dog's faces at least. Another one of the animal's noses was busy sniffing his crotch, while the third looked supremely disinterested. Dean suppressed a yelp and pushed away the nosiest of the dog heads.

The middle head whined and pushed at him. The stupid three-headed dog was roughly the size of an African elephant, but right now it was making four pitiful puppy eyes at him. Dean had to chuckle, scratching it on the head. "Dude, you're fugly, but you're also kinda adorable." He ran his hands over the silky ears, then rubbed underneath two chins. Now the third head was interested, licking at his arm.

Cerberus let out a happy little yelp and wagged its tail, then flopped over on its back. Dean shrugged and reached over to scratch its belly. "Hey, who's a fugly hell puppy? You are!" Now all three heads were panting happily, and Dean scratched harder until one of the dog's back legs was twitching spasmodically. Although he couldn't really tell, Dean could almost swear he saw Charon rolling his eyes.

"Cerberus! Heel!" Hades snapped as he strode back over. The three-headed dog whined but scrambled upright and sat as its master approached. Hades scowled at the dog, then turned to Dean, flourishing a scroll and the orange Get Out Of Hell Free card.

"You made a deal with the Crossroads Demon, agreeing to trade your soul for your brother's life and one year, correct?" Dean nodded. "You agreed to the further stipulation that you would make no attempt to break the deal, the penalty for which would be the forfeiting of your brother's life, correct?"

"Yeah. And my year's up, I didn't try to break the deal. The hellhounds came to get me. So?"

Hades gritted his teeth and slowly, deliberately rolled up the scroll. "Yes. Your soul has been collected and registered in our possession. You have fulfilled the terms of your contract. All that remains is the final delivery into Hell, as per standard crossroads deal clauses." He glared at the orange card. "However, this card is a legal voucher recognized by our claims department. It permits the holder to get out of Hell free. Because it was given to you by another, it has a valid redemption value not in violation of the terms of your contract."

Hades took a deep breath, then punched a hole through the card and handed it back to Dean. "You're free. Get out of Hell. Now."

Dumbly, Dean took the card back and blinked up at Hades. "Umm . . . which way's out?"

* * *

Far away, the Moirae, also known as the Fates, watched the proceedings with interest. When Hades punched the card, Klotho and Lakhesis groaned. 

Atropos smiled to herself and handed the thread back to Klotho, who gave her sister a dirty look before reweaving the cut thread back together.

"That's the second time, Atropos," she grumbled, then turned her ire on Lakhesis. "I thought you said he'd reached the end of his thread."

Lakhesis shrugged, playing idly with her measuring rod. "I thought he had. But remember, these Winchester threads seem to be very elastic. They have a tendency to stretch longer than they should."

"And who's fault is that, spinner?" Atropos pointed out, sharpening her shears. "I believe you both lost the bet."

Her sisters muttered darkly, but fished out the gold coins they'd wagered and dropped them in her hand. She rolled them in her fingers to measure their weight and grinned toothily. "Never bet against the Future, sisters."

* * *

Sam sniffed and blinked away tears, trying to concentrate on driving. Not surprisingly, his thoughts kept fixating on the still body lying in the backseat, bloodstained and cold. The hellhounds had been quick, at least. Dean hadn't suffered. The wounds weren't even that bad. 

But Sam had failed his brother, failed to save him. Dean had always bailed Sam out, even rescued him from death. Now Sam had failed to do the same, even knowing that his brother would end up spending an eternity in hell. Dean was dead. What kind of brother was he?

More tears welled up and spilled down his cheeks before he could force them back. No, he couldn't cry, not now. He had to drive, had to get to Bobby's, take care of Dean's . . . remains.

_Oh God. No, don't think about it yet. Just drive_. Dean would kill him if he crashed the car now.

Sam let out an involuntary broken laugh, choking back sobs. Hell or no, if he crashed the car Dean would find a way to come back to kick his ass. For a second he was almost tempted . . .

Dean sat up in the back seat and yelled, "SONUVABITCH!"

Sam shrieked.

Five minutes later, sitting on the side of the road with the Impala parked haphazardly on the shoulder, one tire up on a rock, Sam's heartbeat finally settled when he examined the orange card he remembered well, now with a neat hole through the center. Dean sat next to him, their shoulders bumping as he used a water bottle and a rag to wipe the worst of the blood smears off his skin.

"So, it actually worked?" Sam murmured wonderingly.

Dean took a final swipe with the rag, then threw it in the back seat. "Yep." He nudged his brother and grinned widely. "Knew you'd do it."

Sam ducked his head, an answering grin spreading uncontrolled over his face until his cheeks ached. Yeah, he'd done it, and all it had taken was a memory and some faith.

And someone's strange sense of humor to actually market those cards.

He flipped the card back to Dean, who slipped it into his wallet. It might be useless for its stated purpose now, but it served just fine as another memory.

Besides, Sam had one of his own in his wallet.

He turned to his brother with a mischievous smirk. "So that makes _how_ many places you've been kicked out of now?"

* * *

A/N: The cards are real; see them at www dot goohf dot com  



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